1. Field of the Invention
The present invention relates to novel N-substituted 3-arylpyrrolidines, processes for their preparation, their use as fungicides, fungicides which contain the novel active ingredients and methods for controlling harmful fungi with these active ingredients.
2. Discussion of the Background
DE 27 27 482 discloses the following arylalkylpyrrolidine derivative as a compound having a fungicidal action. However, its action is unsatisfactory. ##STR2##
We have found that compounds of the formula I ##STR3## where R.sup.1 is 2,2-dimethylpropyl, 3,3-dimethylbutyl, 4,4'-dimethylpentyl, 2,4,4-trimethylpentyl, 6-methylhept-2-yl, 3,5,5-trimethylhexyl, 6,10-dimethylundec-2-yl, 3-methylcyclohexyl, 3,3-dimethylcyclohexyl, 3,3,5-trimethylcyclohexyl, 3,3,5,5-tetramethylcyclohexyl, 4-methylcyclohexyl, 4-ethylcyclohexyl, 4-propylcyclohexyl, 4-isopropylcyclohexyl, 4-tert-butylcyclohexyl, trans-4-tert-butylcyclohexyl, 4-(2-methylbut-2-yl)-cyclohexyl, 4-(2,4,4-trimethylpent-2-yl)-cyclohexyl, cyclododecyl, C.sub.3 -C.sub.9 -trialkylsilyl-substituted C.sub.4 -C.sub.12 -cycloalkyl, 4-hydroxycyclohexyl, 4-hydroxy-3-methylcyclohexyl, 4-hydroxy-3,5-dimethylcyclohexyl, 4-hydroxy-3,3-dimethylcyclohexyl, 4-hydroxy-3,3,5-trimethylcyclohexyl, or C.sub.5 -C.sub.12 -cycloalkenyl which is unsubstituted or substituted by hydroxyl, C.sub.1 -C.sub.9 -alkyl, C.sub.1 -C.sub.5 -alkoxy or C.sub.3 -C.sub.9 -trialkylsilyl, or R.sup.1 is furthermore C.sub.9 -C.sub.11 -bicycloalkyl which is unsubstituted or substituted by hydroxyl, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.5 -alkoxy, C.sub.3 -C.sub.9 -trialkylsilyl, acetoxy, benzoyloxy or benzyloxy, or R.sup.1 is furthermore 4-tert-butylbenzyl, 4-chlorobenzyl, 4-tert-butoxybenzyl, 1,4-dioxaspiro[4,5]dec-8-yl, a 5-membered to 7-membered heterocycloalkyl having 1 or 2 hetero atoms from the group consisting of oxygen and/or sulfur, a 5-membered to 7-membered heterocycloalkylmethyl having 1 or 2 hetero atoms from the group consisting of oxygen and/or sulfur, or a C.sub.1 -C.sub.8 -alkyl-substituted 5-membered to 7-membered heterocycloalkyl or heterocycloalkylmethyl having 1 or 2 hetero atoms from the group consisting of oxygen and/or sulfur, R.sup.2 is C.sub.3 -C.sub.10 -alkyl, C.sub.3 -C.sub.8 -alkoxy or C.sub.3 -C.sub.9 -trialkylsilyl, R.sup.3 is C.sub.1 -C.sub.5 -alkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl or C.sub.7 -C.sub.10 -arylalkyl, X- is a plant-tolerated anion and n is 0 or 1, and their plant-tolerated salts possess an excellent fungicidal action coupled with good toleration by plants.
Salts are understood as salts having a plant-tolerated anion X- of any inorganic or organic acid, for example of hydrochloric acid, hydrofluoric acid, hydrobromic acid, sulfuric acid, phosphoric acid, hydriodic acid, dodecylbenzenesulfonic acid, formic acid, alkylcarboxylic acids, acetic acid, propionic acid, palmitic acid, perfluoroheptanoic acid, oxalic acid, malonic acid, benzoic acid, malic acid, dodecylsulfuric acid, glycerol-2-phosphoric acid, methylsulfuric acid, methanesulfonic acid, p-toluenesulfonic acid or nitric acid, for example the bisulfate and dihydrogen phosphate salts.